4.7 Article

A Highly Enantioselective Catalytic Mannich Reaction of Indolenines with Ketones

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 9, Pages 1715-1718

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300161

Keywords

enantioselectivity; indolenines; ketones; Mannich reaction; regioselectivity

Funding

  1. National Natural Science Foundation of China [21232007, 21172206]
  2. National Basic Research Program of China (973 Program) [2010CB833300]
  3. Program for Changjiang Scholars and Innovative Research Team in University [IRT1189]

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A range of polysubstituted indolenines (3H-indoles) smoothly underwent an L-proline-catalyzed enantioselective Mannich reaction with various ketones in a highly regioselective manner to give structurally diverse 2-acylmethylindolines in good yields with excellent ee. The current study provides a powerful approach for the transformation of unactivated five-membered cyclic aldimines into optically active nitrogen-containing heterocycles with high enantioselectivity.

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